Why is some metaphor bad, and some good?

[elfs]

Quick, which of these is from something critically acclaimed, and which of these is the winner of a "bad writing" award?

• The beetle looked like a cross between an espresso machine and a 1928 Packard.
• For lunch they ate Tapir kabobs, sizzling hot, drowned in a red pepper sauce that the devil used to paint his Bentley.
• Her wet T-shirt clung to her torso like paint on the nose cone of a jumbo jet.

The last is from a "Bad writing" contest; the first two are from Mark Helprin's Memoirs from an Antproof Case, and Helprin is widely regarded as a master of metaphor and simile. I think the last line can be helped with some military imagery, but really, it does its job very well: it accurately conveys a sense of gleaming, precision form-fitting that gets the picture across quite nicely. So why is it "bad writing?"

Comments

[mundens.livejournal.com]

It seems, based on the comments, most people reading it think the woman is being compared to the jet whereas if you read it carefully you'll realize that it is her wet tshirt clinging to her breasts that is being compared to the paint clinging to the nose cone of a jumbo jet.

This is an apt simile, as the nose cone of a jumbo jet is somewhat breast-like, more so than, for example, and as mentioned, a fighter nose cone, which is too sharp and pointed.

But it's bad writing because it lacks clarity, obviously some people require more explanation to understand what the writer intended, it's not bad because of the simile it uses.